title: Antibody-catalyzed decarboxylation and aldol reactions using a primary amine molecule as a functionalized small nonprotein component.
abstract: Catalytic antibody 27C1 bears binding sites for both a substrate- and a functionalized small nonprotein component in the active site. We investigated the possibility of exploiting imine and enamine intermediates using a primary amine molecule into the active site of antibody 27C1. The antibody catalyzed β-keto acid decarboxylation with a rate enhancement (kcat/Km/kuncat) of 140,000, as well as highly regioselective cross-aldol reactions of ketones and p-nitrobenzaldehyde. These studies provide new strategies for the generation of catalytic antibodies possessing binding sites for functionalized components.
authors.affiliation: Department of Biological Science, Graduate School of Science, Osaka Prefecture University, 1-1 Gakuen-cho, Naka-ku, Sakai, Osaka 599-8531, Japan; Department of System Chemotherapy and Molecular Science, Division of Bioinformatics and Chemical Genomics, Graduate School of Pharmaceutical Sciences, Kyoto University, Sakyo, Kyoto 606-8501, Japan.
authors.forename: Fumihiro
authors.initials: F
authors.lastname: Ishikawa
authors.forename: Kouki
authors.initials: K
authors.lastname: Uno
authors.forename: Masao
authors.initials: M
authors.lastname: Nishikawa
authors.forename: Takeshi
authors.initials: T
authors.lastname: Tsumuraya
authors.forename: Ikuo
authors.initials: I
authors.lastname: Fujii
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D000588:Amines / Q000737:chemistry*; D000906:Antibodies / Q000378:metabolism*; D001547:Benzaldehydes / Q000737:chemistry; D001665:Binding Sites; D002384:Catalysis; D020134:Catalytic Domain; D003653:Decarboxylation; D007659:Ketones / Q000737:chemistry; D007700:Kinetics; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; D000588:Amines; D000906:Antibodies; D001547:Benzaldehydes; D007659:Ketones; C029915:4-nitrobenzaldehyde; C116609:3-hydroxybutanal
keywords: Catalytic antibody; Decarboxylation reaction; Enamine mechanism; Regioselective aldol reactions